Reaction Steps
To a solution of (3-(3-pyridyloxy)propyl)methylamine (800.0 mg, 4.81 mmol) in ethanol (12 mL) was added galactaric acid (505.7 mg, 2.41 mmol). Water (2.5 mL) was added dropwise, while gently warming the light-yellow solution. To remove some white, insoluble solids, the warm solution was filtered through a glass wool plug, washing the filter plug with a warm solution of ethanol-water (4:1, v/v) (4 mL). The filtrate was diluted with ethanol (18 mL), producing a white precipitate. The mixture was allowed to cool to ambient temperature and was further cooled at 5° C. for 15 h. The precipitate was filtered, washed with ethanol (6 mL), vacuum dried at 45° C. for 10 h, followed by further vacuum drying at ambient temperature for 48 h to give 994.4 mg (76.1%) of an off-white, crystalline powder, mp 161-165.5° C. FT-IR (powder): 3000 (s, br, O—H of COOH), 3100-2800 (s, br, C—H), 3600-2300 (s, br, C—OH), 1585 (s, COO−), 1422 (s, COO−), 1365 (s, COO−), 1272 (s, C—O, mixed ether), 1230 (m), 1106 (s, C—O, mixed ether), 1045 (s), 808 (w, 3-subst. pyridine), 770 (w), 707 (m, 3-subst. pyridine), 665 (w), 635 (w) cm−1. 1H NMR (D2O, 300 MHz): δ8.27 (s, 1H), 8.19 (d, 1H, J=3.27 Hz), 7.51-7.41 (m, 2H), 4.27 (s, 1H), 4.25 (t, 2H, J=5.70 Hz), 3.97 (s, 1H), 3.30 (t,2H, J=7.18 Hz), 2.78 (s, 3H), 2.24 (p, 2H, J=7.18 Hz). 13C NMR (D2O, 75 MHz): δ182.33, 157.61, 144.41, 139.76, 127.76, 125.60, 74.58, 74.28, 68.73, 49.82, 35.87, 28.17. EI-MS: m/z (relative intensity) 166 (M+, 1.88%), 123 (3.81%), 95 (24.34%), 78 (3.91%), 44 (100.00%).
